I've performed a reaction several times over the past few months, and this is the first time I experienced a new problem. Normally I add diethylenetriamine to acetonitrile to serve as a solution for the first reaction. It is miscible with acetonitrile. The last time I added it the solution turned a bit cloudy. This is certainly abnormal from my experience. Is it possible the acetonitrile was bad? I believe I used an older bottle this time that was sitting around the lab. It could possibly be 10 years old or more. Normally I use newer acetonitrile, but this bottle was handy and I didn't expect any problems. Could the acetonitrile go bad?